Ethyl Propionate → 1-(4-Methyl-1,3-thiazol-2-yl)butan-2-one

反応式

[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.C([Li])CCC.[C:13](OCC)(=[O:16])[CH2:14][CH3:15]>C1COCC1>[CH3:7][C:5]1[N:6]=[C:2]([CH2:1][C:13](=[O:16])[CH2:14][CH3:15])[S:3][CH:4]=1

参加物

反応条件

温度: -78 °C

実験手順

3.00 g (26.5 mmol) of 2,4-dimethylthiazole are dissolved in 30 ml of THF and, at −78° C., 11.6 ml (29.2 mmol) of n-butyllithium (2.5 M solution in hexane) are added dropwise. After stirring at −78° C. for 2 hours, 4.60 g (45.1 mmol) of ethyl propionate are added as solution in 15 ml of abs. THF. The mixture is stirred at −78° C. for 1 h and then warmed to room temperature. It is then hydrolyzed with sodium bicarbonate solution, and the mixture is extracted three times with diethyl ether. The combined organic phases are dried with magnesium sulfate, and the solvent is removed in a rotary evaporator. 3.5 g (39% of theory) of the title compound are obtained in 50% purity (GC-MS) and are employed without further purification.